ECMDB: Dihydroneopterin monophosphate (ECMDB21206) (M2MDB001614)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (2)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:55 -0600

Update Date

2015-06-03 17:20:52 -0600

Secondary Accession Numbers

ECMDB21206

Identification

Name:

Dihydroneopterin monophosphate

Description

Dihydroneopterin monophosphate is a member of the chemical class known as Biopterins and Derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Dihdroneopterin monophosphate is an intermediate involved in tetrahydrofolate biosynthesis and salvage in E. coli. It is converted to 7,8-dihydroneopterin through an unknown phosphorylase enzyme.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphate
2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine phosphoric acid
7,8-Dihydro-D-neopterin 3'-phosphate
7,8-dihydro-D-Neopterin 3'-phosphoric acid
Dihydroneopterin 3'-monophosphate
Dihydroneopterin 3'-monophosphoric acid
Dihydroneopterin 3'-phosphate
Dihydroneopterin 3'-phosphoric acid
Dihydroneopterin monophosphoric acid
Dihydroneopterin-P

Chemical Formula:

C₉H₁₂N₅O₇P

Weight:

Average: 333.1946
Monoisotopic: 333.047434275

InChI Key:

PLSQMGZYOGSOCE-XINAWCOVSA-L

InChI:

InChI=1S/C9H14N5O7P/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-21-22(18,19)20/h4,6,15-16H,1-2H2,(H2,18,19,20)(H4,10,11,13,14,17)/p-2/t4-,6+/m1/s1

CAS number:

Not Available

IUPAC Name:

6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-1,2,7,8-tetrahydropteridin-4-olate

Traditional IUPAC Name:

6-[(1S,2R)-3-(hydrogen phosphonatooxy)-1,2-dihydroxypropyl]-2-imino-7,8-dihydro-1H-pteridin-4-olate

SMILES:

[H][C@@](O)(COP(O)([O-])=O)[C@@]([H])(O)C1=NC2=C(NC1)NC(=N)N=C2[O-]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Heteroaromatic compound
Vinylogous amide
1,2-diol
Ketimine
Secondary alcohol
Azacycle
Secondary amine
Hydrocarbon derivative
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Alcohol
Imine
Organic oxygen compound
Organic nitrogen compound
Amine
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:58762 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	3.29 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-5.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-13	ChemAxon
pKa (Strongest Basic)	15.08	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	205.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.97 m³·mol⁻¹	ChemAxon
Polarizability	27.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Dihydroneopterin triphosphate + Water > Dihydroneopterin monophosphate + Hydrogen ion + Pyrophosphate
Dihydroneopterin monophosphate + Water > 7,8-Dihydroneopterin + Phosphate
7,8-dihydroneopterin 3'-triphosphate + Water > Pyrophosphate + Hydrogen ion + Dihydroneopterin monophosphate

SMPDB Pathways:

Folate biosynthesis	PW000908
GTP degradation	PW001888

KEGG Pathways:

Folate biosynthesis ec00790

EcoCyc Pathways:

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1009000000-35334543f830e03972d5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0032-5119000000-8a1311553ff5e2a2a732	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01qd-9741000000-f826bc486977b4d9a121	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1009000000-a036e9146b5363f6c194	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9002000000-60f9db77669111782949	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003s-9000000000-116e1778470f092edb9c	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	58762
HMDB ID	Not Available
Pubchem Compound ID	25245170
Kegg ID	C05925
ChemSpider ID	26331350
Wikipedia ID	Not Available
BioCyc ID	DIHYDRONEOPTERIN-P
EcoCyc ID	DIHYDRONEOPTERIN-P

Enzymes

Protein Details

1. Dihydroneopterin triphosphate pyrophosphatase

General function:: Involved in dATP pyrophosphohydrolase activity
Specific function:: Catalyzes the hydrolysis of dihydroneopterin triphosphate to dihydroneopterin monophosphate and pyrophosphate. Required for efficient folate biosynthesis. Can also hydrolyze nucleoside triphosphates with a preference for dATP
Gene Name:: nudB
Uniprot ID:: P0AFC0
Molecular weight:: 17306

Protein Details

2. Mutator mutT protein

General function:: Replication, recombination and repair
Specific function:: Involved in the GO system responsible for removing an oxidatively damaged form of guanine (7,8-dihydro-8-oxoguanine) from DNA and the nucleotide pool. 8-oxo-dGTP is inserted opposite dA and dC residues of template DNA with almost equal efficiency thus leading to A.T to G.C transversions. MutT specifically degrades 8-oxo-dGTP to the monophosphate
Gene Name:: mutT
Uniprot ID:: P08337
Molecular weight:: 14927

Reactions

8-oxo-dGTP + H(2)O = 8-oxo-dGMP + diphosphate.

Dihydroneopterin monophosphate (ECMDB21206) (M2MDB001614)

Structure for #<Compound:0x67ad0338>

Enzymes

Reactions